Eastern Massachusetts Beach Vacations 2026

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Top Beach vacation packages in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.

The Mansion at Ocean Edge

$780

per person

Dec 31 - Jan 3

found 1 day ago

Roundtrip non-stop flight included

Chattanooga (CHA) to Boston (BOS)

8.2/10 Very Good! (1,006 reviews)

Harbor View Hotel

$1,014

per person

Dec 25 - Dec 29

found 1 day ago

Roundtrip non-stop flight included

Allentown (ABE) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

Loved the heated saltwater pool. Was disappointed there was not comfortable sitting in the room, esp on a rainy day or not feeling well, and watching a movie. Was surprised no elevator and we were on the third floor. The “grab and go” breakfast option was no more than a few pastries. That was disappointing. For early departure to catch ferry at 0530, no coffee was available.

Reviewed on Oct 22, 2026

The Beachside

Nantucket Town

$2,359

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

Cedar Rapids (CID) to Boston (BOS)

9.4/10 Exceptional! (383 reviews)

Newly renovated beautifully Great location walking distance to download Clean rooms Great staff Great fun room

Reviewed on Oct 22, 2026

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5* Beach vacations in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.

Harbor View Hotel

$1,014

per person

Dec 25 - Dec 29

found 1 day ago

Roundtrip non-stop flight included

Allentown (ABE) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

Reviewed on Oct 22, 2026

Don't see what you're looking for?

See all available trips from Columbus to Eastern Massachusetts

View all trips

3 Night Beach vacations in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.

The Mansion at Ocean Edge

$780

per person

Dec 31 - Jan 3

found 1 day ago

Roundtrip non-stop flight included

Chattanooga (CHA) to Boston (BOS)

8.2/10 Very Good! (1,006 reviews)

The Beachside

Nantucket Town

$2,359

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

Cedar Rapids (CID) to Boston (BOS)

9.4/10 Exceptional! (383 reviews)

Newly renovated beautifully Great location walking distance to download Clean rooms Great staff Great fun room

Reviewed on Oct 22, 2026

Harbor View Hotel

$1,917

per person

Nov 25 - Nov 28

found 8 hours ago

Roundtrip non-stop flight included

Indianapolis (IND) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

Reviewed on Oct 22, 2026

Don't see what you're looking for?

See all available trips from Columbus to Eastern Massachusetts

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4 Night Beach vacations in Eastern Massachusetts

Price found within the past 48 hours. Click for updated prices.

By the Sea Guests Bed & Breakfast & Suites

$847

per person

Dec 25 - Dec 29

found 1 day ago

Roundtrip non-stop flight included

Allentown (ABE) to Boston (BOS)

9.2/10 Wonderful! (250 reviews)

Wonderful stay. Enjoyed the beach. Great breakfast. Great staff. Seemed well run.

Reviewed on Oct 19, 2026

Harbor Hotel Provincetown

Save 100% on your flight

$18,192

per person

Dec 11 - Dec 15

found 1 day ago

Roundtrip non-stop flight included

Pensacola (PNS) to Provincetown (PVC)

8.4/10 Very Good! (1,005 reviews)

Chatham Tides

$1,070

per person

Dec 25 - Dec 29

found 1 day ago

Roundtrip non-stop flight included

Allentown (ABE) to Boston (BOS)

9.4/10 Exceptional! (778 reviews)

You can’t beat the location! Beautiful, peaceful setting!

Reviewed on Oct 21, 2026

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See all available trips from Columbus to Eastern Massachusetts

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How do I book the best Eastern Massachusetts beach vacation packages?

Life’s a beach when you dive into our brilliant Eastern Massachusetts beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Eastern Massachusetts?

A rental steps from the shore creates an amazingly affordable Eastern Massachusetts beach vacation. Seaside sojourns during low season start from $780. Prices and availability are subject to change. Additional terms may apply.

When should I book a Eastern Massachusetts beach holiday?

For a bustling beach break, book in . For a less crowded coast, is the time to turn up.

How can I book the best family beach vacations in Eastern Massachusetts?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Eastern Massachusetts beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Eastern Massachusetts vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Eastern Massachusetts beach vacation deals?

Sort your search results by deals to delight in amazing Eastern Massachusetts beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Eastern Massachusetts beach trip with free cancellation and/or flexible dates?

Just like the Eastern Massachusetts tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Eastern Massachusetts beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Eastern Massachusetts. (OK, maybe not that last part.)

Top Beach Eastern Massachusetts Hotels

Sea Crest Beach Resort

350 Quaker Rd North Falmouth MA

2 hours drive from Fenway Park

At this hotel, get ready to enjoy the sunsets on the beach in North Falmouth, as you'll be near Cape Cod Beaches. 2 restaurants, a private beach, and a beach ...

Lighthouse Inn

1 Lighthouse Inn Rd West Dennis MA

2 hours drive from Fenway Park

Make the most of this fantastic location, as you'll be a short walk from Cape Cod Beaches with a holiday at this hotel. Amenities at Lighthouse Inn include a ...

Chatham Bars Inn

297 Shore Rd Chatham MA

2 hours drive from Fenway Park

Settle in and relax at this luxury boutique resort and get ready to stroll along the shore in Chatham, as you'll be a short walk from Cape Cod Beaches. 3 outdoor ...

9.2/10 Wonderful! (873 reviews)

Travelers like: on the beach, cabanas, beach bars, beach umbrellas

Travelers say...

"Amazing property and staff."

Reviewed on Oct 18, 2026

See all 16,050 properties in Eastern Massachusetts

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.